Anthranilic Acid → 2-(Octanoylamino)benzoic acid

HRID 1417862

Reaction equation

HRID 1417862 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].N1C=[CH:15][CH:14]=[CH:13][CH:12]=1.[Cl-].Cl.[O:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1>>[C:20]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([OH:10])=[O:9])(=[O:19])[CH2:21][CH2:22][CH2:23][CH2:12][CH2:13][CH2:14][CH3:15]

Participants

6

Reactant 5

HCID 227Anthranilic AcidHCID 312ChlorideHCID 313Hydrochloric AcidHCID 1049PyridineHCID 8028Tetrahydrofuran2×

Product 1

HCID 41572202-(Octanoylamino)benzoic acidYield 79.4%

Procedure

Anthranilic acid was dissolved in a mixed solvent containing pyridine and tetrahydrofuran (THF) in 5:5 ratio and a THF solution of n-caprioyl chloride was dropped to the solution during several hours for reaction. After the reaction, hydrochloric acid was added to the reaction mixture. Pyridine hydrochloride was filtered and the solvent was removed. N-n-octanoylanthranilic acid was obtained from the remaining reactant after the purification by column chromatography with the yield of 79.4%.

Workup

  1. additionwas added to the reaction mixture
  2. filtrationPyridine hydrochloride was filtered
  3. customthe solvent was removed

Sources & evidence

ORD record
ord-b8104d869cdb44e8956dd7976acec3d1
Source dataset
uspto-grants-1999_03
Patent number
USRE036138

Linked notes

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